Before Samir Khan’s jihadist dreams came to a sudden fiery end, he insisted, in his first interview with the national news media, that he had done nothing wrong.

“I’ve never told anybody to build bombs,” he said.

Story Continued Below

Two years after that interview, the Saudi-born U.S. citizen of Pakistani heritage would publish the most influential bomb-making manual since The Anarchist Cookbook. And two years after that, he would be dead at age 25, vaporized by Hellfire missiles fired by a drone launched from his country of birth. It was the first targeted assassination of an American citizen abroad in U.S. history, executed on Sept. 30, 2011, a few weeks past the 10th anniversary of 9/11. By then, Khan had already shown himself to be an uncommonly gifted propagandist. He spread the message of jihad to a generation of young English-speaking recruits like him, and laid a blueprint for waging holy war from behind your computer screen.

President Obama called the drone strike “a major blow to al-Qaeda’s most active operational affiliate,” in large part because the missile had managed, somewhat to the surprise of intelligence officials, to kill Khan as well as the intended target, American-born cleric Anwar al-Awlaki and two others. But as successful as the attack seemed at the time, its long-term effectiveness seems far less certain. Indeed, al-Awlaki’s sermons, not to mention the how-to horrors of Khan’s manual, have proven much harder to kill.

Police have yet to say whether they believe Ahmad Rahami, the alleged bomber who injured 39 people in New York and New Jersey with homemade explosives earlier this month, was influenced by Khan’s writing. But it’s hard not to see Khan’s imprint in the two types of explosives used, and the three interconnected pipe bombs (for maximum blast effect) found next to the Seaside Park running route, as if ripped from the pages of his first issue of Inspire in July 2010. It’s impossible to quantify the reach of Khan’s illustrated guide, but its residue has been spotted in the Boston Marathon case, the San Bernardino attacks, and a planned 2012 attack on Fort Hood. The magazine has also been cited as inspiration in several ISIS-related cases now winding their way through the courts, like that of two self-described “bad bitches” from Queens who were allegedly plotting a way to make a bomb.

Khan’s remarkably durable message traces its roots to a middle-class community in Charlotte. A decade before Congress held hearings on online radicalization, Khan quietly sat in his parents’ basement, tapping out the posts to one of the first jihadi blogs in existence under the username Inshallahshaheed—God willing, a martyr. Khan proclaimed allegiance to Osama bin Laden, published a propaganda zine, and corresponded with al-Awlaki, the al-Qaeda cleric whom he would later join in the battlefields of Yemen. Al-Awlaki would soon become the first American to grace President Barack Obama’s hand-picked “kill list.”. A U.S. official said in 2010 that Awlaki was working “actively to kill Americans, so it's both lawful and sensible to try to stop him.”

The month they were killed, the FBI wrote that the duo “craft a radicalizing message tailored to American Muslims.”A web counter had ranked Khan’s blog in the top 1 percent of most popular sites worldwide.

In the years after the drone strike the sermons and Khan’s manual only extended their audience. Awlaki’s Youtube sermons, still a touchstone for so many would-be jihadis in the United States today, seemed to grow more potent after he was killed, extrajudicially, by the “enemy” he battled for the moral upper hand. And, because he died before the bitter split between ISIS and al-Qaeda, the newest generation of keyboard warriors, still claims him as their own. But it is Samir Khan, his protégé, who paved the way for an army of jihadist bloggers, posting about faraway wars from cozy beds in middle-class homes like the one he grew up in, and who laid out their blueprint for terror attacks that continue to this day.

Khan, who classmates at W.T. Clarke High School would later remember as just a regular guy, moved to Long Island with his parents when he was seven years old. But as he grew older, Khan gravitated towards the more radical reaches of Islam, later refusing to say the Pledge of Allegiance and describing himself as a “mujahid” in his high school yearbook. A move to Charlotte, North Carolina, didn’t seem to help; nor did his parents’ attempts to unplug the internet or interventions by community leaders, recalls Jibril Hough, a local activist who knew the family and served as their spokesman in 2011. “Usually, no one has the opportunity to counsel them,” he says. “This time was different.”

Over a few years, Khan fine-tuned the art of mass-produced English-language jihadi agitprop, beginning with his blog and a magazine called Jihad Recollections. Later he took it to another level with Inspire’s more overt calls to violence. At the time, his blog was immensely popular in jihadist circles, a “uniquely Samir Khan product” for the time, according to Seamus Hughes, deputy director of George Washington University’s Program on Extremism.“There was nothing else like it.” He wrapped theological arguments in familiar colloquial English, designed to reach an audience that might not be deeply schooled in Islam. Khan had the advantage of being first to the gate on his side, and Jihad Recollectionsattracted a who’s-who of writers who would later serve time for terror offenses.

“We have worked very hard to get his web sites shut down but to no avail,” an FBI agent in DC lamented to a colleague in Charlotte in 2007. “He pops up again in another spot.”

Before long, Khan’s online activities attracted local news media. The New York Times and a local TV station profiled him in 2007. To the Times reporter he seemed like an “unlikely foot soldier in what Al Qaeda calls the ‘Islamic jihadi media.’” Khan denied recruiting for Al Qaeda to the local TV station, but told the Times he hoped to one day meet Osama bin Laden. Most photos that exist of Khan today, excluding a yearbook picture and a handful of beaming photos taken in Yemen before his death, are stills from that local segment, with Khan in a polo shirt outside his parents’ house, hair pulled back in a greasy bun. “I think that was a turn because he lost his job[at a customer care company] and then he started spending more time at home,” Hough said. “And shortly after that time, he started making plans to go to Yemen.”

Unlike al-Awlaki, who had spent his adolescence in Sanaa in Yemen, Khan had no personal ties to the country. Like the young people who blog on Tumblr and skirt the line between preaching and propaganda on Twitter today, he was caught up in the fervor of a battleground for a new world order. And he was among the first to tell those who came up after him that it was their religious duty to go abroad.

In one of the issues of Inspire he published from Yemen, he declared himself “proud to be a traitor to America.”

"America, take a hint for once: maybe you did something,” he wrote.

Khan’s family avoided media attention after he was killed, only acquiescing to a brief statement they passed along through a spokesperson, condemning an execution without a trial. (They abhorred his militancyand recruited imams to deradicalize him; records show his parents were registered Republicans. The Khans didn’t respond to interview requests for this story.) They later joined the al-Awlaki family in an unsuccessful lawsuit against the U.S. government over the deaths, and that of al-Awlaki’s 16-year-old son in a different strike months later, but have otherwise stayed out of the spotlight. The publicity was rough on the parents, who were raising two other children. “Any time [the father’s] name would pop up on a Google search, it would be hard for him to keep employment,” Hough says.

The family was haunted by the question of what their son did to deserve such an end. Khan had been impeccably precise in avoiding arrest while he was still in the U.S., reportedly even hiring a lawyer to divine the fine line between free speech and inciting violence. FBI files released after Khan’s death show the agency was actively seeking shreds of evidence that Khan broke the law, and that agents recommended “all work done in this case should be focused towards finding a resolution, i.e. a disruption via an arrest/prosecution.” They discussed arrest plans at one point, but the plan was abandoned, and Khan continued to straddle the line between thought and deed.

“And it’s not against the law until you act on something,” Hough says. “And he never did. He never did commit any crime.”

Fifteen years into the War on Terror, the FBI and Department of Justice might disagree. The organizations have become aggressive, even overly so, some say, about prosecuting terrorist sympathizers for material support to a foreign terrorist organization—a catch-all term that can cover anything from providing a gift card to FBI agents posing as ISIS to helping a friend buy a plane ticket for his route to Raqqa. If Khan didn’t commit a crime by propagandizing, the intent to board a plane bound for al- Qaeda territory in Yemen would almost certainly meet the bar under the Obama administration’s current guidelines. At the very least, he’d probably get nabbed for communicating a threat across state lines, Hughes says.

But if the bar to prosecution has gotten progressively lower, it has not managed to scare off some of Khan’s peers. After his death, they took up his mantle, shifting platforms but mimicking his mission of transforming esoteric jihadi screeds into English-language sound bytes. To date, the Department of Justice has charged more than 100 people with ISIS-related crimes. Many are related to the internet—blogs and social media that relay the messages of Awlaki and Khan in hopes of inspiring supporters to rise up.

“What’s interesting about Samir is that he went from being a propagandist to a planner,” Hughes says. “Here’s a guy who took his thoughts and turned them into actions, and showed it could be done.”

And that might be a legacy Khan would have only hoped for. He wrote in Inspire, five years before the ISIS caliphate would convince young people it was their duty to come spread the jihadi message, that his greatest wish was to die fighting and planting the flag of his version of Islam.

"And how reputable, adventurous and pleasurable is such a life compared to those who remain sitting, working from nine to five?”